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Single in the Second City? Here are tips for LGBTQ+ dating in Chicago 

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Jul 21, 2023

Single in the Second City? Here are tips for LGBTQ+ dating in Chicago 

There are two things I’m most passionate about in this world — being gay and loving Chicago. 

I love it here. I love my home. I love my community. I love my library. I love my knitting. But when I’m alone, it can feel nebulous to find my people. Like any city, Chicago is better shared. 

I’ve been in these streets, and some days it’s tough to date! But the payoff is amazing, sometimes for friends, sometimes for relationships, and sometimes just for swapping stories of being queer and never meeting again. 

Whether you’re trying to take things off the apps, trying for a meet-cute with your neighbor in a queer-friendly area, or just need some gay friends, there are endless ways to meet other gay women and nonbinary folks around you. 

Check out these neighborhoods, events, and date ideas to fall in love with Chicago’s queer community. And if you ever need advice, just knock three times on the Bean, and I’ll appear in your reflection, your gay Chicago fairy godmother. Go forth, my beautiful Chicago queers! 

The gayborhoods of Chicago 

By now, you’ve probably noticed I’m biased, but Chicago has some of the best LGBTQ+ friendly neighborhoods in the country. Here are some places to consider if you’re looking for an apartment. 

So, we’re going to be talking about Chicago’s queerest neighborhoods, like:

  • Andersonville
  • Logan Square
  • Wicker Park 
  • Northalsted
  • South Side


Source: Wikimedia Commons

Andersonville — where lesbians go to retire at 25. That’s my pitch for their neighborhood slogan. 

Andersonville, once known as Girlstown, is home to many queer-women-owned establishments such as the bar Nobody’s Darling, the bookstore Women and Children First, and the sex shop Early To Bed. What else could you need?

And it’s a great place to live with beautiful Chicago row houses and tree-lined streets. It’s directly adjacent to The Riviera, the Aragon Theatre, and our lovely Lake Michigan. 

Logan Square 

Source: Wikipedia

Spend 10 minutes on HER, and you’ll be like, “Why do all these girls and theys live in Logan?” 

Logan Square has amazing restaurants, robust nightlife, and plenty of independent retailers that sell everything you need for your lesbian hobbies. Some places that have queer vibes: Lost Girls Vintage, The Owl Bar, and of course, the Logan Square Farmers Market.

Sometimes you spend enough time in Logan Square and forget that straight people exist at all. 

Wicker Park 

Source: Wikimedia Commons

Wicker Park is another west-side neighborhood where all my friends live. New trendy shops, restaurants, and cafes are always popping up, and it has one of the best farmer’s markets in the city. You can see why the gays love her. 

It also has my favorite vegan Mexican restaurant (Quesadilla La Reina del Sur) and my favorite burger in Chicago (Sault). And it’s where I get all my tattoos!


Source: Reddit

Northalsted is kind of a neighborhood-in-a-neighborhood nestled in Lakeview. But beware — next to the gayest spot in town is the straightest spot in town, Wrigleyville. Just kidding! Straight people don’t bite. You’ll be fine. 

In 2020, Boystown was renamed to Northalsted to be more gender inclusive. Sometimes it still feels like a predominately white, gay man space, but I’ve had some of my fondest, queerest Chicago memories here. There’s nothing like reading Samantha Irby’s new book and being like, “I’ve also taken an explosive shit in the Berlin bathroom!” 

The Pride Parade takes place here every year, as well as Market Days. Halsted Street is bustling with gay bars and boasts some great restaurants. 

Don’t write off the South Side!   

Source: Facebook

The South Side is my home, and I’ve found some of my favorite queer events here at places like Promontory Point in Hyde Park or Ping Tom Memorial Park in Chinatown. Neighborhoods like Hyde Park and Bronzeville are great places to live, especially for queer people of color who have always existed on the South Side. 

There’s Brave Space Alliance, one of the most well-known LGBTQ organizations in the city, which is based in Hyde Park. At the end of June, Chicago Black Pride hosted the fifth Pride South Side and is planning more events throughout the year. 

Decades of redlining have left large swaths of the south side cut off from the things some Chicagoans take for granted, like public transportation or walkability. Black and Brown communities in Chicago face systemic barriers to community organizing, but that has never stopped them. Chicago’s BIPOC organizers literally invented the game! 

Where do I meet lesbians in Chicago? Check out these events

Chicago lesbians loveee a meet-up. With only two dedicated lesbian bars in the city, organizers have worked tirelessly to bring the community together. Follow them on socials and bring a trusted wing person to one of these events. 

Let’s get to know the holy trinity of sapphic events in Chicago:

  • Lez Get Together
  • The Queer Social Club
  • B. Blyss

Lez Get Together

Lez Get Together is a new event series aiming to connect queer women outside of bars.  In their own words: “Lez Get Together is on a mission to curate spaces beyond the bar scene. We are expanding our community’s options for gathering by designing booze-free spaces where friendship, connection, and community are at the forefront.” 

They’ve hosted six events so far, and they’re a blast! I will admit I was intimidated to go from seeing Instagram pics of so many hot queers in one room. 

But I’m so glad I did! I was less focused on dating, although my head was turning left and right, but I had been feeling lonely in my 20s and wanted to find more queer friends. People were warm and eager to connect, and the whole room was lit up with queer joy. 

The Queer Social Club

The Queer Social Club is another great option for a wide variety of events organized by queer women and nonbinary people for women and nonbinary people. They have beach days, plant swaps, art parties, stitch nights, happy hours, DJ nights, and field days — there’s truly something for everyone. At their Maker’s Market last year, I met someone who sells amazing houseplants and got some gorgeous earrings. Just beautiful vibes all around! 

B. Blyss

B. Blyss has been organizing cultural events in Chicago since 2004, specifically geared toward BIPOC queer people. They host brunches, performances, DJs, and plenty of pride events across the city throughout the year. Check them out before the summer is over!

Very queer, very Chicago date ideas

Now I’m really giving away my best material here, but I care about y’all. Chicago is a huge city with a billion things to do, and planning dates can be so stressful when it’s two queer people trying to be as accommodating as possible. 

Here are some ideas to get you started!

  • Walking through Andersonville 
  • Picnic at the Museum Campus 
  • The Garfield Park Conservatory 

Walking through Andersonville 

Source: Facebook

Clark Street in Andersonville is a place for a date. I know, I know. There are loads of options for brunch, coffee, drinks, or dinner — but they all have very different vibes. Just trust! 

Women and Children’s First, a bookstore owned by self-proclaimed trans-inclusive feminists, is a perfect place to stop along the way. It has a great selection of queer literature, and — fun fact — it inspired the Feminist Bookstore Portlandia sketch. 

Picnic at the Museum Campus 

Source: Wikimedia Commons

Many straight people will have picnics here, but this is our chance to queer the space. The Museum Campus has one of my favorite views of Chicago. On a grassy hill facing North, you can see from the tip of Navy Pier to Willis Tower. You can bike there on the lakefront trail or walk under the 10th Street bridge. It’s just a magical place. 

The Garfield Park Conservatory 

Source: Catherine Henderson

It’s 10 degrees, -4 with windchill, and you haven’t seen the sun for a month.  You are desperate for human connection. You have managed to ask out a beautiful girl, but you don’t want to freeze to death. The Garfield Park Conservatory is the perfect option for a date in Chicago winter!

The Conservatory is beautifully maintained, with half a dozen rooms filled with different types of plants from around the world. Wander hand-in-hand, staring up at palms that reach the ceiling, fruit trees of all kinds, aloe plants in bloom, and ferns that are older than dinosaurs. And it’s free, though you must reserve a time on their website in advance. 

I’m just really passionate about Chicago and queer women. But for real, I know it’s tough out there sometimes. I’m rooting for you, and Chicago is rooting for you too. 

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Catherine Henderson is a journalist based in Chicago. She has worked at a wide variety of newsrooms, including The Denver Post, Chalkbeat, Business Insider and In These Times, covering education, career development and culture. Catherine holds a master’s and bachelor’s degree in journalism from Northwestern University. Outside of work, she enjoys traveling, exploring Chicago, reading LGBTQ lit, and analyzing internet trends.

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